New prenylated indole alkaloids from fungus Penicillium sp. derived of mangrove soil sample

Yang, Bin; Dong, Jianhua; Lin, Xiuping; Zhou, Xuefeng; Zhang, Yanying; Liu, Yonghong

doi:10.1016/j.tet.2014.04.043

Cited by 41 publications

(29 citation statements)

References 40 publications

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“…Since this species already produces the Penicillium and Aspergillus metabolite penicillic acid, 126 there is a possibility that the fungus was indeed correctly identified as a Penicillium or Aspergillus . Most of these unique prenylated indole alkaloids are produced by both Aspergillus and Penicillium species except that the mangrovamides, 127 brevianamides, chrysogenamide, paraherquamides and marcfortines have only been reported from Penicillium species, while the asperparalines, sclerotiamides, notoamides, versicolamides, avrainvillamides, stephacidins, and taichunamides have been recorded from Aspergillus species. However, chemotaxonomic investigations have shown that the mangrovamides and okaramines have been found in both genera (Frisvad, unpublished data).…”

Section: Fungal Producers Of Prenylated Indole Alkaloidsmentioning

confidence: 99%

Structural and stereochemical diversity in prenylated indole alkaloids containing the bicyclo[2.2.2]diazaoctane ring system from marine and terrestrial fungi

et al. 2018

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Various fungi of the genera Aspergillus, Penicillium, and Malbranchea produce prenylated indole alkaloids possessing a bicyclo[2.2.2]diazaoctane ring system. After the discovery of distinct enantiomers of the natural alkaloids stephacidin A and notoamide B, from A. protuberus MF297-2 and A. amoenus NRRL 35660, another fungi, A. taichungensis, was found to produce their diastereomers, 6-epi-stephacidin A and versicolamide B, as major metabolites. Distinct enantiomers of stephacidin A and 6-epi-stephacidin A may be derived from a common precursor, notoamide S, by enzymes that form a bicyclo[2.2.2] diazaoctane core via a putative intramolecular hetero-Diels–Alder cycloaddition. This review provides our current understanding of the structural and stereochemical homologies and disparities of these alkaloids. Through the deployment of biomimetic syntheses, whole-genome sequencing, and biochemical studies, a unified biogenesis of both the dioxopiperazine and the monooxopiperazine families of prenylated indole alkaloids constituted of bicyclo[2.2.2]diazaoctane ring systems is presented.

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Section: Fungal Producers Of Prenylated Indole Alkaloidsmentioning

confidence: 99%

Structural and stereochemical diversity in prenylated indole alkaloids containing the bicyclo[2.2.2]diazaoctane ring system from marine and terrestrial fungi

et al. 2018

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“…They bear a γ-methyl proline derived skeleton, unprecedented among the paraherquamide family. Mangrovamides did not show cytotoxicity against the human tumor cell lines H1975, U937, K562, BGC823, MOLT-4, MCF-7, A549, HeLa, HL-60 and Huh-7, while mangrovamide C ( 216 ) displayed moderate inhibitory effect on AChE (IC 50 58.0 μM) [ 142 ].…”

Section: Marine Indole Alkaloidsmentioning

confidence: 99%

Marine Indole Alkaloids

2015

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Marine indole alkaloids comprise a large and steadily growing group of secondary metabolites. Their diverse biological activities make many compounds of this class attractive starting points for pharmaceutical development. Several marine-derived indoles were found to possess cytotoxic, antineoplastic, antibacterial and antimicrobial activities, in addition to the action on human enzymes and receptors. The newly isolated indole alkaloids of marine origin since the last comprehensive review in 2003 are reported, and biological aspects will be discussed.

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“…In the course of our study on marine derived microbes, several active metabolites were isolated [ 13 , 14 , 15 , 16 ]. In our previous study, two aromatic butyrolactones were reported from the same fungus, A. flavipes [ 17 ].…”

Section: Introductionmentioning

confidence: 99%

New Meroterpenoids from the Endophytic Fungus Aspergillus flavipes AIL8 Derived from the Mangrove Plant Acanthus ilicifolius

et al. 2015

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Four new meroterpenoids (2–5), along with three known analogues (1, 6, and 7) were isolated from mangrove plant Acanthus ilicifolius derived endophytic fungus Aspergillus flavipes. The structures of these compounds were elucidated by NMR and MS analysis, the configurations were assigned by CD data, and the stereochemistry of 1 was confirmed by X-ray crystallography analysis. A possible biogenetic pathway of compounds 1–7 was also proposed. All compounds were evaluated for antibacterial and cytotoxic activities.

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New prenylated indole alkaloids from fungus Penicillium sp. derived of mangrove soil sample

Cited by 41 publications

References 40 publications

Structural and stereochemical diversity in prenylated indole alkaloids containing the bicyclo[2.2.2]diazaoctane ring system from marine and terrestrial fungi

Structural and stereochemical diversity in prenylated indole alkaloids containing the bicyclo[2.2.2]diazaoctane ring system from marine and terrestrial fungi

Marine Indole Alkaloids

New Meroterpenoids from the Endophytic Fungus Aspergillus flavipes AIL8 Derived from the Mangrove Plant Acanthus ilicifolius

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